Dihydrofuran carboxamides

ABSTRACT

The invention concerns novel dihydrofuran carboxamides of formula (I), ##STR1## in which R stands for groups of formulae (a), (b) or (c), ##STR2## in which R 1 , R 2 , R 3 , X, m, n and p have the meanings given in the description. The invention also concerns a process for preparing the novel substances, and their use for combating undesirable micro-organisms for plant- and material-protection purposes.

This application is a 371 of PCT/EP97/03693 filed Jul. 7, 1997.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to novel dihydrofuran-carboxamides, to aprocess for their preparation and to their use as microbicides.

BACKGROUND OF THE INVENTION

It is already known that certain dihydrofurancarboxanilides havefungicidal properties (cf. DE-A 1 914 954 and J. Pesticide Sci. 18(1993), 245-251). Thus, for example,2-methyl-4,5-dihydrofuran-3-carboxanilide and2-methyl-4,5-dihydrofuran-3-N-(1,1,3-trimethyl-indan-4-yl)-carboxamidecan be used for controlling fungi. The activity of these compounds isgood, but in some cases leaves something to be desired at lowapplication rates.

DETAILED DESCRIPTION OF THE INVENTION

This invention, accordingly, provides novel dihydrofuran-carboxamides ofthe formula ##STR3## in which R represents groupings of the formulae##STR4## in which R¹ represents optionally substituted cycloalkyl,optionally substituted bicycloalkyl, optionally substitutedcycloalkenyl, optionally substituted cycloalkylalkyl, optionallysubstituted aryl, optionally substituted aroxy, optionally substitutedaralkyl or represents alkyl,

X represents alkyl having 1 to 6 carbon atoms, halogen, cycloalkylhaving 3 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms orhalogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms,

m represents integers from 0 to 3,

R² represents alkyl, cycloalkyl, optionally substituted aryl oroptionally substituted aralkyl,

n represents integers from 0 to 3,

R³ represents alkyl, cycloalkyl, optionally substituted aryl oroptionally substituted aralkyl and

p represents integers from 0 to 3.

Furthermore, it has been found that dihydrofuran-carboxamides of theformula (I) are obtained when 2-methyl-4,5-dihydrofuran-3-carbonylhalides of the formula ##STR5## in which Hal represents chlorine orbromine,

are reacted with amines of the formula

    H.sub.2 N--R                                               (III)

in which

R is as defined above,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent.

Finally, it has been found that the novel dihydrofuran-carboxamides ofthe formula (I) have very good microbicidal properties and can beemployed for controlling undesirable microorganisms both in cropprotection and in the protection of materials.

Surprisingly, the dihydrofuran-carboxamides according to the inventionhave considerably better fungicidal activity than2-methyl-4,5-dihydrofuran-3-carboxanilide and2-methyl-4,5-dihydrofuran-3-N-(1,1,3-trimethylindan-4-yl)-carboxamide,which are constitutionally similar prior-art active compounds of thesame direction of action.

The formula (I) provides a general definition of thedihydrofuran-carboxamides according to the invention.

R preferably represents the groupings of the formulae ##STR6## in whichR¹ preferably represents cycloalkyl having 3 to 8 carbon atoms which isoptionally mono- to trisubstituted by identical or different alkylgroups having 1 to 4 carbon atoms, represents bicycloalkyl having 7 to12 carbon atoms which is optionally mono- to trisubstituted by identicalor different alkyl groups having 1 to 4 carbon atoms, representscycloalkenyl having 5 to 8 carbon atoms which is optionally mono- totrisubstituted by identical or different alkyl groups having 1 to 4carbon atoms or represents cycloalkylalkyl having 3 to 8 carbon atoms inthe cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety whichis optionally mono- to trisubstituted by identical or different alkylgroups having 1 to 4 carbon atoms, or

represents phenyl which may be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms, or

represents phenoxy which may be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms, or

represents phenylalkyl having 1 to 4 carbon atoms in the alkyl moietywhich may be mono- to trisubstituted in the phenyl moiety by identicalor

different substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms,

or represents straight-chain or branched alkyl having 1 to 12 carbonatoms,

X preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluorine, chlorine, bromine, cycloalkyl having 3 to 8carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbonatoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms or represents halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,

m preferably represents the numbers 0, 1 or 2,

R² preferably represents straight-chain or branched alkyl having 1 to 12carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms or represents phenylalkyl having 1 to 4carbon atoms in the alkyl moiety which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen and alkyl having 1 to 4 carbon atoms,

n preferably represents the numbers 0, 1, 2 or 3,

R³ preferably represents straight-chain or branched alkyl having 1 to 12carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms or represents phenylalkyl having 1 to 4carbon atoms in the alkyl moiety which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen and alkyl having 1 to 4 carbon atoms and

p preferably represents the numbers 0, 1, 2 or 3.

Particular preference is given to dihydrofuran-carboxamides of theformula (I) in which

R represents a grouping of the formula ##STR7## in which R¹ representscycloalkyl having 3 to 8 carbon atoms which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of methyl, ethyl, n-propyl, isopropyl and tert-butyl,or represents bicycloalkyl having 7 to 12 carbon atoms which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of methyl, ethyl,n-propyl, isopropyl and tert-butyl, or

represents cycloalkenyl having 5 to 8 carbon atoms which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of methyl, ethyl, n-propyl, isopropyl andtert-butyl, or represents cycloalkylalkyl having 3 to 8 carbon atoms inthe cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety whichis optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of methyl, ethyl,n-propyl, isopropyl and tert-butyl, or

represents phenyl which may be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl and tert-butyl, or

represents phenoxy which may be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl and tert-butyl, or

represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moietywhich may be mono- to trisubstituted in the phenyl moiety by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl andtert-butyl, or

represents straight-chain or branched alkyl having 1 to 12 carbon atoms,

X represents methyl, ethyl, n-propyl, isopropyl, tert-butyl, fluorine,chlorine, bromine, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, methoxy, ethoxy, trichloromethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl, trifluoromethoxy ordifluoromethoxy,

m represents the numbers 0, 1 or 2, where X represents identical ordifferent radicals if m represents 2,

R² represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl,iso-butyl, tert-butyl, 2-ethyl-butyl, octyl, decyl, dodecyl,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenylwhich is optionally mono- or disubstituted by fluorine, chlorine,bromine, methyl, ethyl, n-propyl, isopropyl and/or tert-butyl orrepresents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety,where the phenyl moiety may be mono- or disubstituted by fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl and/or tert-butyl,

n represents the numbers 0, 1, 2 or 3, where R² represents identical ordifferent radicals if n represents 2 or 3,

R³ represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl,iso-butyl, tert-butyl, 2-ethyl-butyl, octyl, decyl, dodecyl,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenylwhich is optionally mono- or disubstituted by fluorine, chlorine,bromine, methyl, ethyl, n-propyl, isopropyl and/or tert-butyl orrepresents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety,where the phenyl moiety may be mono- or disubstituted by fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl and/or tert-butyland

p represents the numbers 0, 1, 2 or 3, where R³ represents identical ordifferent radicals if p represents 2 or 3.

Using 2-methyl-4,5-dihydrofuran-3-carbonyl chloride and4-fluoro-2-cyclooctyl-aniline as starting materials, the course of theprocess according to the invention can be illustrated by the equationbelow. ##STR8##

The formula (II) provides a general definition of the2-methyl-4,5-dihydrofuran-3-carbonyl halides required as startingmaterials for carrying out the process according to the invention. Halalso preferably represents chlorine or bromine.

The 2-methyl-4,5-dihydrofuran-3-carbonyl halides are known or can beprepared by known methods (cf. DE-A 1 914 954 and Chem. Ber. 104 (1971),734-738).

The formula (III) provides a general definition of the amines requiredas reaction components for carrying out the process according to theinvention. In this formula, R preferably has those meanings which havealready been mentioned as being preferred for this radical in connectionwith the description of the compounds of the formula (I) according tothe invention.

The amines of the formula (III) are known or can be prepared by knownprocesses (cf. U.S. Pat. No. 5,223,526, EP-A 0 545 099, EP-A 0 589 301and DE-A 44 45 545).

Suitable acid binders for carrying out the process according to theinvention are all inorganic and organic bases which are customary forsuch reactions. Preference is given to using alkaline earth metal oralkali metal hydroxides, such as sodium hydroxide, calcium hydroxide,potassium hydroxide, or else ammonium hydroxide, alkali metalcarbonates, such as sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate, alkali metal or alkaline earth metalacetates such as sodium acetate, potassium acetate, calcium acetate, andalso tertiary amines, such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU). However, it isalso possible to carry out the reaction without an additional acidbinder, or to employ an excess of amine component, so that itsimultaneously acts as acid binder.

Suitable diluents for carrying out the process according to theinvention are all customary inert organic solvents. Preference is givento using optionally halogenated aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichloroethane or trichloorethane; ethers, such as diethyl ether,diisopropyl ether, methyl-t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate; sulphoxides, such as dimethyl sulphoxide or sulphones, such assulpholane.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between 0° C. and 100° C.,preferably between 10° C. and 80° C.

The process according to the invention is generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure.

When carrying out the process according to the invention, generally 1mol or else an excess of amine of the formula (III) and 1 to 3 mol ofacid binder are employed per mole of2-methyl-4,5-dihydrofuran-3-carbonyl halide of the formula (II).However, it is also possible to employ the reaction components in otherratios. Work-up is carried out by customary methods. In general, thereaction mixture is mixed with water and the organic phase is separatedoff and, after drying, concentrated under reduced pressure. The residuethat remains can, if required, be freed of any impurities that may stillbe present using customary methods, such as chromatography orrecrystallization.

The compounds according to the invention have a potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed [lacuna] crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae,

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Altemaria species, such as, for example, Altemaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

The active compounds according to the invention can be employedparticularly successfully for controlling diseases in fruit andvegetable growing and viticulture, such as, for example, againstVenturia, Podosphaera, Phytophtora and Plasmopara species. They are alsovery successfully used for controlling rice diseases, such as, forexample, Pyricularia species.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, papers and boards, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants and/or foam formers.In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. The following aremainly suitable as liquid solvents: aromatics, such as xylene, tolueneor alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, alcohols, such as butanol or glycol andtheir ethers and esters, ketones, such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents, suchas dimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning thoseliquids which are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants, such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals, suchas kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth and ground synthetic minerals, such as highlydisperse silica, alumina and silicates. Suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, or else syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.Suitable emulsifiers and/or foam formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or elseprotein hydrolysates. Suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients, such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations also mixed with known fungicides, bactericides,acaricides, nematicides or insecticides in order thus, for example, towiden the spectrum of action or to prevent development of resistance. Inmany cases, synergistic effects are achieved, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of co-components in mixtures are the following compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimnidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-alumninium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,imninoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G, OK-8705, OK-8801,2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide,2,6-dichloro-N-(4-trifluorormethylbenzyl)-benzamide, 2-aminobutane,2-phenylphenol (OPP), 8-hydroxyquinoline sulphate,cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,bis-(-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide, O-methylS-phenyl phenylpropylphosphoramidothioate,N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone-O-(phenylmethyl)-oxime,N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,methanetetrathiol sodium salt,2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N'-methoxy-methanimidamide,α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,N-formyl-N-hydroxy-DL-alanine sodium salt,N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,ethyl[(4-chlorophenyl)-azo]-cyanoacetate,N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide, methylN-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,spiro[2H]-1-benzopyrane-2,1'(3'H)-isobenzofuran]-3'-one, methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate, potassiumhydrogen carbonate,1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,2-bromo-2-(bromomethyl)-pentanedinitrile,2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimnidine-5-carbonitrile,methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate, S-methyl1,2,3-benzothiadiazole-7-carbothioate,N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide,8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, betacyluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699 chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen, quinalphos,

RH 5992

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth regulators.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bypouring, spraying, atomizing, spreading, dusting, foaming, brushing onand the like. It is further possible to apply the active compounds bythe ultra-low volume method or to inject the preparation of activecompound, or the active compound itself, into the soil. The seed of theplants can also be treated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range: They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

In the treatment of seed, amounts of active compound of from 0.001 to 50g, preferably 0.01 to 10 g, are generally required per kilogram of seed.

In the treatment of the soil, active compound concentrations of from0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight,are required at the site of action.

The compositions used for the protection of industrial materialsgenerally comprise an amount of from 1 to 95%, preferably from 10 to75%, of the active compounds.

The use concentrations of the active compounds according to theinvention depend on the species and the occurrence of the microorganismsto be controlled and on the composition of the material to be protected.The optimal rate of application can be determined by test series. Ingeneral, the use concentrations are in the range from 0.001 to 5% byweight, preferably from 0.05 to 1.0% by weight, based on the material tobe protected.

It is possible to increase the activity and the activity spectrum of theactive compounds which are to be used according to the invention in theprotection of materials, or of the compositions, concentrates or quitegenerally formulations which can be prepared from these, by adding, ifappropriate, other compounds having antimicrobial action, fungicides,bactericides, herbicides, insecticides or other active compounds forincreasing the activity spectrum or for obtaining special effects suchas, for example, additional protection against insects. These mixturesmay have a wider activity spectrum than the compounds according to theinvention.

The preparation and the use of the compounds according to the inventionare illustrated by the examples below.

PREPARATION EXAMPLES Example 1 ##STR9##

At room temperature, a solution of 1.5 g (0.01 mol) of2-methyl-4,5-dihydrofuran-3-carbonyl chloride in 10 ml of toluene isadded dropwise with stirring to a mixture of 2.2 g (0.01 mol) of4-fluoro-2-cyclooctylaniline, 1.0 g of triethylamine and 40 ml oftoluene. After the addition has ended, the reaction mixture is stirredat room temperature for another 2 hours. The reaction mixture issubsequently admixed with water. The organic phase is separated off,dried over sodium sulphate and then concentrated under reduced pressure.The residue that remains is stirred with hexane. The resultingcrystalline product is filtered off with suction and dried at 50° C.under reduced pressure. In this manner, 2.2 g (66.7% of theory) ofN-(4-fluoro-2-cyclooctyl)-2-methyl-4,5-dihydrofuran-3-carboxanilide areobtained in the form of a solid substance of melting point 91° C.

The dihydrofuran-carboxamides of the formula (I) listed in the Tablebelow are prepared in a similar manner.

                  TABLE 1                                                         ______________________________________                                                                       (I)                                             ##STR10##                                                                    Example No.                                                                           R                   Physical constant                                 ______________________________________                                         2                                                                                     ##STR11##          m.p.: 91° C.                                3                                                                                     ##STR12##          m.p.: 104° C.                               4                                                                                     ##STR13##          m.p.: 123° C.                               5                                                                                     ##STR14##          m.p.: 65° C.                                6                                                                                     ##STR15##          m.p.: 104° C.                               7                                                                                     ##STR16##          m.p.: 73° C.                                8                                                                                     ##STR17##          m.p.: 151° C.                               9                                                                                     ##STR18##          .sup.1 H-NMR*  δ = 2.30(s, 3H)              10                                                                                     ##STR19##          m.p.: 143° C.                              11                                                                                     ##STR20##          m.p.: 132° C.                              12                                                                                     ##STR21##          m.p.: 231° C.                              13                                                                                     ##STR22##          .sup.1 H-NMR*  δ = 2.28(s, 3H)              14                                                                                     ##STR23##          m.p.: 161° C.                              15                                                                                     ##STR24##          m.p.: 156° C.                              16                                                                                     ##STR25##          m.p.: 84° C.                               17                                                                                     ##STR26##          .sup.1 H-NMR*  δ = 2.31(s, 3H)              18                                                                                     ##STR27##          m.p.: 117° C.                              19                                                                                     ##STR28##          m.p.: 86° C.                               20                                                                                     ##STR29##          .sup.1 H-NMR*  δ = 2.29(s, 3H)              21                                                                                     ##STR30##          .sup.1 H-NMR*  δ = 2.18(s, 3H)              22                                                                                     ##STR31##          m.p.: 221° C.                              23                                                                                     ##STR32##          .sup.1 H-NMR*  δ = 2.28(s, 3H)              24                                                                                     ##STR33##          m.p.: 116° C.                              25                                                                                     ##STR34##          m.p.: 123° C.                              26                                                                                     ##STR35##          m.p.: 170° C.                              27                                                                                     ##STR36##          m.p.: 121° C.                              28                                                                                     ##STR37##          m.p.: 108° C.                              29                                                                                     ##STR38##          m.p.: 90° C.                               30                                                                                     ##STR39##          .sup.1 H-NMR*  δ = 2.16(s, 3H)              31                                                                                     ##STR40##          m.p.: 113° C.                              32                                                                                     ##STR41##          .sup.1 H-NMR*  δ = 2.16(s, 3H)              33                                                                                     ##STR42##          m.p.: 107° C.                              34                                                                                     ##STR43##          .sup.1 H-NMR*.sup.)  δ = 2.23(s, 3H)        35                                                                                     ##STR44##          m.p.: 118° C.                              36                                                                                     ##STR45##          m.p.: 165° C.                              37                                                                                     ##STR46##          .sup.1 H-NMR*  δ = 2.22(s, 3H)              38                                                                                     ##STR47##          m.p.: 145° C.                              39                                                                                     ##STR48##          .sup.1 H-NMR*  δ = 2.24(s, 3H)              40                                                                                     ##STR49##          m.p.: 83° C.                               41                                                                                     ##STR50##          .sup.1 H-NMR*  δ = 2.23(s, 3H)              42                                                                                     ##STR51##          m.p.: 107-109° C.                          ______________________________________                                         *The .sup.1 HNMR spectra were recorded in deuterochloroform (CDCl.sub.3)      using tetramethylsilane (TMS) as internal standard. Stated is the chemica     shift as δ value in ppm.                                           

*) The ¹ H-NMR spectra were recorded in deuterochloroform (CDCl₃) usingtetramethylsilane (TMS) as internal standard. Stated is the chemicalshift as δ value in ppm.

USE EXAMPLES

In the following examples, the compounds listed below were employed ascomparative substances: ##STR52##2-methyl-4,5-dihydrofuiran-3-carboxanilide (Known from DE-A 1 914 954)##STR53##2-methyl-4,5-dihydrofuran-3-N-(1,1,3-trimethylindan-4-yl)-carboxamide(Known from J. Pesticide Sci. 18 (1993), 245-251)

Example A

Botrytis Test (bean)/Protective

Solvent 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, 2 small agar pieces overgrown with Botrytis cinerea areplaced onto each leaf. The inoculated plants are placed in a dark humidchamber at 20° C.

3 days after the inoculation, the size of the infected areas on theleaves is determined and expressed in %. 0% means an efficacy whichcorresponds to that of the control, while an efficacy of 100% means thatno infection is observed.

Active compounds, active compound concentrations and test results areshown in the Table below.

                  TABLE A                                                         ______________________________________                                        Botrytis test (bean)/protective                                                                     Efficacy in % at an                                                           active compound                                                               concentration in the                                    Active compound       spray liquor of 100 ppm                                 ______________________________________                                        Known                                                                          ##STR54##            57                                                       ##STR55##            33                                                      According to the invention:                                                    ##STR56##            94                                                       ##STR57##            92                                                      ______________________________________                                    

Example B

Erysiphe Test (wheat)/Protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminisf.sp. tritici.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a realtive atmospheric humidity of approximately 80% topromote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means than no infection is observed.

Active compounds, active compound concentrations and test results areshown in the Table below.

                  TABLE B                                                         ______________________________________                                        Erysiphe test (wheat)/protective                                                                    Efficacy in % at an                                                           application rate of active                              Active compound       compound of 250 g/ha                                    ______________________________________                                        Known                                                                          ##STR58##            27                                                      According to the invention                                                     ##STR59##            73                                                      ______________________________________                                    

Example C

Sphaerotheca Test (cucumber)/Protective

Solvent: 47 parts by weight of acetone

Emulgator: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are dusted with conidia of the fungusSphaerotheca fuliginea.

The plants are subsequently placed in a greenhouse at 23 to 24° C. andat a relative atmospheric humidity of approximately 75%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the Table below.

                  TABLE C                                                         ______________________________________                                        Sphaerotheca test (cucumber)/protective                                                              Efficacy in % at an                                                           active compound con-                                                          centration in the spray                                Active compound        liquor of 100 ppm                                      ______________________________________                                        Known                                                                          ##STR60##             25                                                     According to the invention                                                     ##STR61##             77                                                      ##STR62##             62                                                      ##STR63##             75                                                      ##STR64##             70                                                      ##STR65##             50                                                     ______________________________________                                    

Example D

Venturia Test (apple)/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are inoculated with an aqueous conidiasuspension of the causative organism of apple scab Venturia inaequalisand then remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at 20° C. and a relativeatmospheric humidity of approximately 70%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the Table below.

                  TABLE D                                                         ______________________________________                                        Venturia test (apple)/protective                                                                   Efficacy in % at an active                                                    compound concentration in                                Active compound      the spray liquor of 100 ppm                              ______________________________________                                        Known                                                                          ##STR66##           71                                                       According to the invention                                                     ##STR67##           86                                                        ##STR68##           97                                                       ______________________________________                                    

Example E

Material Protection Test

Inhibition of the growth of wood-destroying Basidiomycetes

Solvent: Dimethyl sulphoxide

To produce a suitable preparation of active compound, 0.2 parts byweight of active compound are admixed to 99.8 parts by weight of theabovementioned solvent.

An agar, prepared by using malt extract peptone, is mixed in a liquidstate with the preparation of active compound at the application ratedesired in each case. After solidification, the resulting nutrientmedium is incubated at 27° C. with mycel pieces punched out of coloniesof Basidiomycetes.

Evaluation is carried out after 3- or 7-day storage at 27° C. bymeasuring the growth of the mycelium and scoring the resultinginhibition in per cent in comparison to the untreated control. 0% meansan inhibition of growth which corresponds to that of the untreatedcontrol, while an inhibition of growth of 100% means that no growth ofmycelium is observed.

Active compounds, active compound concentrations and test results areshown in the Table below.

                  TABLE E                                                         ______________________________________                                        Inhibition of the growth of wood-destroying Basidiomycetes                                    Inhibition in per cent of the radial                                          growth of giant colonies at 6 ppm of                                          active compound according to                                                  Example                                                       Fungal species  (28)        (42)                                              ______________________________________                                        Gloeophyllum trabeum                                                                          50          60                                                Coniophora puteana                                                                            50          60                                                Poria placenta  30          50                                                Lentinus tigrinus                                                                             70          80                                                Coriolus versicolor                                                                           70          100                                               Stereum sanguinolentum                                                                        70          80                                                ______________________________________                                    

What is claimed is:
 1. Dihydrofuran-carboxamides of the formula##STR69## in which R represents groupings of the formulae ##STR70## inwhich R¹ represents optionally substituted cycloalkyl, optionallysubstituted bicycloalkyl, optionally substituted cycloalkenyl,optionally substituted cycloalkylalkyl, optionally substituted aryl,optionally substituted aroxy, optionally substituted aralkyl orrepresents alkyl,X represents alkyl having 1 to 6 carbon atoms, halogen,cycloalkyl having 3 to 8 carbon atoms, alkoxy having 1 to 6 carbonatoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atomsor halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, mrepresents integers from 0 to 3, R² represents alkyl, cycloalkyl,optionally substituted aryl or optionally substituted aralkyl, nrepresents integers from 0 to 3, R³ represents alkyl, cycloalkyl,optionally substituted aryl or optionally substituted aralkyl and prepresents integers from 0 to
 3. 2. Dihydrofuran-carboxamides of theformula (I) according to claim 1, in whichR represents the groupings ofthe formulae ##STR71## in which R¹ represents cycloalkyl having 3 to 8carbon atoms which is optionally mono- to trisubstituted by identical ordifferent alkyl groups having 1 to 4 carbon atoms, representsbicycloalkyl having 7 to 12 carbon atoms which is optionally mono- totrisubstituted by identical or different alkyl groups having 1 to 4carbon atoms, represents cycloalkenyl having 5 to 8 carbon atoms whichis optionally mono- to trisubstituted by identical or different alkylgroups having 1 to 4 carbon atoms or represents cycloalkylalkyl having 3to 8 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms inthe alkyl moiety which is optionally mono- to trisubstituted byidentical or different alkyl groups having 1 to 4 carbon atoms,orrepresents phenyl which may be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms, or represents phenoxy which may bemono- to trisubstituted by identical or different substituents selectedfrom the group consisting of halogen and alkyl having 1 to 4 carbonatoms, or represents phenylalkyl having 1 to 4 carbon atoms in the alkylmoiety which may be mono- to trisubstituted in the phenyl moiety byidentical or different substituents selected from the group consistingof halogen and alkyl having 1 to 4 carbon atoms, or representsstraight-chain or branched alkyl having 1 to 12 carbon atoms, Xrepresents straight-chain or branched alkyl having 1 to 4 carbon atoms,fluorine, chlorine, bromine, cycloalkyl having 3 to 8 carbon atoms,straight-chain or branched alkoxy having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms or represents halogenoalkoxy having 1 or 2 carbonatoms and 1 to 5 fluorine, chlorine and/or bromine atoms, m representsthe numbers 0, 1 or 2, R² represents straight-chain or branched alkylhaving 1 to 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms,phenyl which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms or represents phenylalkyl having 1 to 4carbon atoms in the alkyl moiety which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen and alkyl having 1 to 4 carbon atoms, nrepresents the numbers 0, 1, 2 or 3, R³ represents straight-chain orbranched alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 8carbon atoms, phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen and alkyl having 1 to 4 carbon atoms or representsphenylalkyl having 1 to 4 carbon atoms in the alkyl moiety which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms and p represents the numbers 0, 1, 2 or
 3. 3.Process for preparing dihydrofuran-carboxamides of the formula (I)according to claim 1, characterized in that2-methyl-4,5-dihydrofuran-3-carbonyl halides of the formula ##STR72## inwhich Hal represents chlorine or bromine,are reacted with araines of theformula

    H.sub.2 N--R                                               (III)

in whichR is as defined above,if appropriate in the presence of an acidbinder and if appropriate in the presence of a diluent.
 4. Amicrobicidal composition, comprising at least onedihydrofuran-carboxamide of the formula (I) according to claim 1 and oneor more extenders and/or surfactants.
 5. A method for controllingundesirable microorganisms in crop protection and in the protection ofmaterials, comprising the step of applying a dihydrofuran-carboxamide ofthe formula (I) according to claim 1 to the microorganisms and/or theirhabitat.